Phenolic acid profiles of Chinese wheat cultivars

Phenolic acid concentrations were determined in 37 Chinese commercial winter wheat cultivars grown at a single site over two seasons, and fractions comprising free and bound types were analyzed using HPLC with measurements of individual phenolic acids in each fraction. Most of the parameters were significantly influenced by cultivar, season, and their interaction effects, with cultivar variance being predominant. Wide ranges of concentration among the 37 cultivars were observed. The average concentration of bound type was 661 μg g⁻¹ of dm, making up 97.5% of the phenolic acid determined with ferulic accounting for 70.7% of it, while free type made up only 2.5% of the phenolic acid determined with syringic accounting for 44.7% of it. Bound type was the predominant source to the grain phenolic acid concentrations determined. There were highly significant and positive correlations between bound ferulic concentration and total bound phenolic acid concentration, and between free syringic concentration and total free phenolic acid concentration. Cultivars Liangxing 66 and Zhongmai 895 were stable in concentration of components of phenolic acids across seasons, with high values of free and bound phenolic acids indicating they could be selected as parents in wheat breeding for health beneficial phenolic acid.     

Phenolic Compounds in Wheat Grain Cultivars

Three hydroxybenzoic acids: p-hydroxybenzoic acid, vanillic acid and syringic acid; six hydroxycinnamic acids: p-coumaric acid, ferulic acid and four ferulic acid derivatives and a flavonoid (apigenin) were identified and quantified in 34 accessions corresponding to 19 cultivars of wheat applying HPLC coupled to diode array detector. Considerable differences between the wheat cultivars were observed in the phenolic contents. Some cultivars (Colorado, Del País, Barbilla, Jallado, Raspinegro Canario and Plaganudo) could be selected according to the high levels of phenolic compounds. Ferulic acid was the major phenolic acid compound followed by syringic and p-hydroxybenzoic acids. The proportion of ferulic acid present as dimeric forms ranged from 4.2 to 8.6% across all of the wheat cultivars analyzed. Apigenin, p-hydroxybenzoic and syringic acids did not show significant correlations. Many correlations between the determined hydroxycinnamic acids were observed. The ferulic acid and all the ferulic acid derivatives showed highly significant correlations, suggesting that the concentrations of diferulic acids depend on the concentration of ferulic acid.     

Determination of phenolic acid concentrations in wheat flours produced at different extraction rates

High-performance liquid chromatography (HPLC) was used to determine the distribution of phenolic acids in wheat flours produced from five milling extraction rates ranging from 60% to 100% in four cultivars sown in two locations in the 2008–2009 season. Considerable variation was observed in free and bound phenolic acids, and their components in flours with different extraction rates. Most phenolic acids, including the component ferulic, were present in the bound form (94.0%). Ferulic (51.0%) was the predominant phenolic acid in wheat grain, and caffeic (22.8%) and p-coumaric (17.6%) acids were abundant. The phenolic acids and their components were all significantly influenced by effects of cultivar, milling, location, and cultivar × milling interaction, with milling effect being the predominant. The proportions of phenolic compounds varied considerably among milling extractions and cultivars, and their levels depended on both initial grain concentrations and on selection of milling extraction that was incorporated into the final product. The grain phenolic acid concentrations determined ranged from 54 μg g⁻¹ in flour produced at 60% extraction rate to 695 μg g⁻¹ in flour produced at 100% extraction rate, indicating their higher concentrations in bran associated with cell wall materials. Therefore, wholemeal wheat products maximize health benefits and are strongly recommended for use in food processing.     

Effect of baking on free and bound phenolic acids in wholegrain bakery products

Phenolic compounds, particularly ferulic acid the most abundant phenolic in wheat, are the major contributors to the in vitro antioxidant capacity. They are present in wheat in free and bound forms which affect their bioavailability. Thus the current study aims to investigate changes in free and bound phenolic acids occurred during baking in wholegrain bread, cookie and muffin. The products were also fortified with lutein due to its proved health benefits, and were previously evaluated with regard to lutein stability and bioavailability and antioxidant properties. The control and fortified wholegrain bakery products contained reasonable amounts of free and bound phenolic acids with bread products exhibiting the highest level per serving (0.6 and 11.7 mg, respectively). Ferulic acid was the principal phenolic both in the free or bound extracts of the three products followed by p-coumaric acid in the bound extracts. Baking resulted in an increase in free phenolic acids in the three products, while bound phenolic acids decreased in bread and slightly changed in cookie and muffin products. Though the effect of baking appeared to be dependent on type of baked product, type of phenolic, recipe and baking conditions, the wholegrain products should be considered good sources of phenolic antioxidants.     

Phenolic acids composition,total polyphenols content and antioxidant activity of Triticum monococcum, Triticum turgidum and Triticum aestivum: A two-years evaluation

Wheat is a good source of polyphenols, plant metabolytes with beneficial effects on human health. However, little information is available on phenolic acid composition and concentration in different Triticum species, as well as on possible environmental effects. To shed some light on this issue, thirty-nine wheat accessions cropped for two years and belonging to different Triticum species (Triticum monococcum, Triticum turgidum ssp. dicoccum, turanicum and durum, Triticum aestivum ssp. spelta and aestivum) were assessed for phenolic acids (ferulic, p-coumaric, vanillic, syringic, p-hydroxybenzoic, caffeic acids and syringaldehyde), total polyphenols and antioxidant activity in soluble conjugated and insoluble bound extracts. Ferulic acid was the most abundant compound in both extracts. Insoluble bound phenolic acids represented >90% of total phenolic acids. Einkorn showed the maximum concentration of conjugated phenolic acids (50.5 mg/kg DM), while durum and bread wheats presented the highest content of bound phenolic acids (651.8 and 629.2 mg/kg DM, respectively). Cropping year influenced the concentration of conjugated but not of bound phenolic acids. A survey of phenolic acid distribution in the kernel showed that they are rare in endosperm, but abundant in germ and bran. Total polyphenols and antioxidant activity were highly correlated to phenolic acid content.     

镍处理下水稻酚酸和酚多聚物含量的变化与白叶枯病诱导抗性的关系

 研究了镍处理下水稻叶片中总酚、酚酸、酚多聚物积累和细胞壁结合态过氧化物酶（POD）活性的变化。镍处理导致总酚含量显著上升,检测到10种可溶性酚酸和7种结合态酚酸。镍处理下可溶性绿原酸和水杨酸含量明显上升,而它们的结合态含量变化不明显;镍处理显著提高可溶性和结合态阿魏酸的含量,显著降低可溶性丁香酸和对 香豆酸的含量,却诱导其结合态含量增加。镍处理后酚多聚物明显积累,以阿魏酸和丁香醛为底物的细胞壁结合态POD的活性显著升高。这些结果结合以前的研究提示,酚酸和酚多聚物积累参与了镍诱导的水稻对白叶枯病的抗性。     

Phenolic Compounds as Cultivar- and Variety-distinguishing Factors in Some Plant Products

The aim of the study was to determine whether phenolic compounds in some varieties of buckwheat, winter and spring barley and peas can be used as factors which distinguish selected cultivars and varieties of plant material. It was observed that the content of total phenolics might be useful as a cultivar-distinguishing factor for all the plant materials analyzed, but it was a distinguishing factor for only some varieties. Individual cultivars and varieties were best distinguished by the content of syringic acid. The levels of syringic and vanillic acids were in reverse proportion to the total amount of phenolics soluble in methanol and a positive correlation between syringic and ferulic acid was observed. Moreover, the protein content of plant material was analyzed and a significant (p ≤ 0.05) correlation between this component and ferulic and vanillic acids was noted.     

Effect of genetic variation on phenolic acid and policosanol contents of Pegaso wheat lines

Total phenolic acid and policosanol contents and compositions of bran from an Italian bread wheat variety Pegaso and its 11 near-isogenic lines were measured. The near-isogenic wheat lines differed at one or more loci coding for storage proteins. The genetic variation included deletions, additions and/or combinations of variations. Almost 95% or more of phenolic acids were in the bound form. Ferulic acid was the predominant bound phenolic acid present in wheat bran samples. Other phenolic acids were p-coumaric, vanillic and syringic acids. Tetracosanol, docosanol, hexacosanol, octacosanol, tricosanol and heneicosanol were found as major policosanol compounds in their decreasing order. Highly significant genotypic differences were observed in total phenolic acid and policosanol concentrations. None of the genetic lines had higher phenolic acid contents than the parent line Pegaso, whereas some of the lines had more policosanol levels. In general, both total phenolic acid composition and contents were higher with genetic lines that varied at Glu-1 loci with 2+Dy high molecular weight glutenin subunit (HMW-GS) (Pegaso 184), variation at Gli-D2 loci (Pegaso 219) and single null A1 (variation at Gli-1/Glu-3 loci; Pegaso 30). Highest total policosanol content was observed with the double null at Glu-A1/Glu-D1 loci (Pegaso 236). These findings may lead to new opportunities for wheat breeders and eventually commercial wheat growers to promote the production of wheat with enhanced levels of health beneficial compounds.     

市售香蕉 15 种酚酸化合物含量的分析

为了探明香蕉中酚酸化合物的种类及含量,本研究采用超高效液相色谱串联质谱（UPLC-MS/MS）法对 香蕉果肉样品进行分析,并对色谱、质谱条件进行优化。结果表明,香蕉富含多种酚酸化合物,且酚酸化合物主 要以游离酯型和结合型存在。含量较高的 2 种酚酸为异阿魏酸（112.54~370.34 μg/g）、阿魏酸（83.96~157.54 μg/g）。 酚酸含量由高至低依次为异阿魏酸>阿魏酸>对香豆酸>3,5-二羟基苯甲酸>芥子酸>香草酸>咖啡酸>对羟基苯甲 酸>鞣花酸>丁香酸>反式肉桂酸>水杨酸。方法验证结果表明该方法检出限低、线性范围宽、灵敏度高,定量结 果准确、可靠,适用于实际样品检测;香蕉样品酚酸组分与含量检测结果可为香蕉的营养成分和功能活性物质 评价提供参考。     

Inhibition of polygalacturonase and polygalacturonic acid lyase fromErwinia carotovora subsp.carotovora by phenolics in vitro

Summary The phenolic acids benzoic, caffeic, chlorogenic, ferulic, p-coumaric, protocatechuic, salicylic, sinapic, syringic and vanillic together with vanillin, were tested for their ability to inhibit polygalacturonic acid lyase (PL) and polygalacturonase (PG) in culture filtrates ofErwinia carotovora subsp.carotovora. None of the compounds inhibited PL at 200 μg/ml, although syringic and sinapic acids caused a 54% and 43% reduction respectively at 400 μg/ml. PG was strongly inhibited by caffeic acid (57% inhibition at 100 μg/ml) and chlorogenic acid caused slight inhibition. Little if any inhibition of PG was caused by benzoic, ferulic, p-coumaric, protocatechuic, salicylic, sinapic, syringic, and vanillic acids or vanillin. The percentage inhibition of PG by chlorogenic acid was not affected by pH values over the range 4–7.     

Changes in Phenolic Compounds in Garlic (<Emphasis Type="Italic">Allium sativum</Emphasis> L.) Owing to the Cultivar and Location of Growth

The contents of total phenolic compounds, flavonoids, and phenolic acids were determined in selected garlic cultivars grown at four locations. The total phenolic content varied from 3.4 mg gallic acid equivalents (GAE)/g of dry matter (dm) to 10.8 mg GAE/g of dm with a mean value of 6.5 mg GAE/g of dm. The myricetin, quercetin, kaempferol, and apigenin flavonoids were not detected in any of the samples. Caffeic acid and ferulic acid were the major phenolic acids found with mean values of 2.9 mg/kg of dm and 2.6 mg/kg of dm, respectively. The mean contents of vanillic, p-hydroxybenzoic, and p-coumaric acids were comparable (0.4–0.8 mg/kg of dm), and the level of sinapic acid was negligible (< 0.1 mg/kg of dm). There was a significant effect of location but an insignificant effect of genotype on contents of caffeic, vanillic, p-hydroxybenzoic, and p-coumaric acids. However, genotype but not location affected the contents of total phenolics and ferulic acid. On average, the white garlic cultivars and Chinese garlic cultivars contained higher contents of total phenolics and ferulic acid than the purple garlic cultivars. However, the differences in the total phenolic content between the purple and white garlic cultivars were not significant.     

Chemical composition and profile characterisation of pumpkin (Cucurbita maxima) seed oil

Seeds of a Tunisian variety (Béjaoui) of pumpkin (Cucurbita maxima) were analysed for their main chemical composition and for their oil properties. Expressed on dry weight basis, seed moisture was 8.46%, whereas contents of proteins, fibre, ash, fat, and total sugars established at 33.92%, 3.97%, 21.97%, 31.57%, and 0.11% respectively. Gas chromatography revealed that the major fatty acids were oleic, linoleic, and palmitic acids (44.11%, 34.77%, and 15.97% respectively). Seed oil was also found to be rich in tocopherols with a predominance of δ-tocopherol (42.27%). The sterol marker β-sisosterol accounted for 39.6% of total sterols contained in seed oil of this variety. Six phenolic acids (protocatechuic, caffeic, syringic, vanillic, p-coumaric and ferulic) were detected, the syringic acid being predominant (7.96 mg/100 g). As a whole, based on its seed oil features, pumpkin may be considered as a valuable source for new multi-purpose products for industrial, cosmetic, and pharmaceutical utilisation.     

Phenolics in the bran of waxy wheat and triticale lines

The present study was designed to determine total phenolic acid contents (TPC) and compositions of bran from newly developed near-isogenic waxy wheat and triticale translocation lines. Two waxy wheat sets, Svevo (durum) and N11 (bread wheat), consisting of partial and waxy null lines and four sets of triticales (GDS7, Trim, Rhino and Rigel) having translocations at 1A.1D and 1R.1D with high molecular weight glutenin subunits (HMW-GS) 5 + 10 and 2 + 12 were investigated. Similar to non-waxy wheat, ferulic acid was the predominant phenolic acid found in waxy wheats analyzed. Two other major phenolics include p-coumaric and vanillic acids followed by lesser quantities of syringic acid. Waxy lines had higher TPC than the parent line in the N11 set, whereas the Svevo set showed the opposite trend. TPC of waxy bread wheats were correlated with amylose fractions in which the order was complete waxy < double waxy nulls < single waxy nulls. Lines with HMW-GS 2 + 12 have lower TPC than other lines in each group of triticales, except the Trim set. TPC was negatively correlated (r = −0.41; p > 0.1) with bran yields in triticale lines studied, indicating that variation in phenolics was not only due to bran yields but also to genotypic differences.     

茶树品种、加工工艺、季节对乌龙茶品质影响的研究

研究了茶树品种、加工工艺和季节对乌龙茶品质的影响,结果表明：鲜叶中醇系香气总量有明显的季节性差异,游离态为春季>夏季>秋季,键合态为春季>秋季>夏季;加工过程中,游离态和键合态醇系香气成分呈现不同的动态变化趋势;茶多酚逐渐减少,游离氨基酸含量先增后减,可溶性糖则与氨基酸相反。对干茶样进行感官审评,春茶后期和夏茶前期槠叶种重做青所制茶样具有明显的乌龙茶品质特征。     

Quantities of phenolic compounds and their impacts on the perceived flavour attributes of rye grain

The use of whole grain rye products, beneficial to one's health, could be substantially extended if the typical intensively bitter flavour of rye could be modified without losing the characteristic rye-like flavour. The aim of the study was to evaluate the contribution of non-volatile phenolic compounds on the perceived flavour. Rye grain was milled into five milling fractions. The levels of phenolic compounds, i.e. the phenolic acids, alkylresorcinols and lignans, of the fractions were analysed and related statistically to sensory flavour profiles by partial least-squares (PLS) regression. The non-bound (free) phenolic acids are suggested to be most flavour-active. Cereal and intense flavour and aftertaste were related to vanillic and veratric acids, alkylresorcinol C_23:0, and other lignans except for pinoresinol. The perceived bitterness of the bran fractions was suggested to result from pinoresinol and syringic acid. Sinapic and ferulic acids, alkylresorcinols, except for alkylresorcinol C_23:0, and syringaresinol seemed to cause the germ-like flavour. Phenolic acids, alkylresorcinols and lignans distributed with a similar pattern in the rye grain as the flavour attributes: the phenolic compounds were clearly located in the outer bran fractions being intense in flavour, but not in the mild-tasting inner layers of the grain.     

Influence of phenolic acid content on sensory perception of bread and crackers made from red or white wheat

Despite the health benefits of wholegrain, consumer acceptance of wholegrain products remains an issue due to the presence of characteristic flavours that some consumers consider to be unacceptable. It was hypothesized that phenolic acids could be contributing to the perceived unacceptable flavours described in wholegrain products. The purpose of this study was to examine the relationship between total phenolic acid content (TPAC) and phenolic acids as quantified by HPLC, to the sensory properties of wholegrain products using partial least squares (PLS) mapping. Red and white wheat flours were investigated in an intermediate (bread) and low (cracker) moisture product system. Red and white wheat demonstrated different phenolic acid profiles despite having similar TPAC. Within the bread crumb, the free and bound phenolic acids provided the best predictive scores; whereas only bound phenolic acids provided high predictive scores in crackers. This suggests that the contribution of phenolic acids to flavour characteristics of wholegrain products varies depending upon the product moisture.     

Relative amounts of tissues in mature wheat (Triticum aestivum L.) grain and their carbohydrate and phenolic acid composition

Hand dissection of mature grains from two common wheats (Triticum aestivum L., cv. Caphorn and cv. Crousty) were performed to quantitatively assess their tissue composition and to obtain homogeneous samples of embryonic axis, scutellum, starchy endosperm, aleurone layer, hyaline layer, outer pericarp and a composite layer made up of testa+hyaline layer+inner pericarp. Polymeric neutral sugar and phenolic acid contents of the samples were determined and used to identify specific composition patterns in each tissue irrespective of the cultivar. The scutellum and embryonic axis showed the lowest amount of carbohydrates with similar relative amounts of arabinose and xylose (Ara+Xyl), but the scutellum differed from the embryonic axis in its high phenolic acid, in particular ferulate dehydrodimer, content. The peripheral layers of the grains were mainly composed of cell wall polysaccharides, chiefly arabinoxylans but with differing structures. The hyaline layer was mostly composed of arabinoxylan with extremely low Ara/Xyl ratio (0.1), with high amounts of ferulic acid monomers and hence very weakly crosslinked. The aleurone layer differed from the outer pericarp by its much lower Ara/Xyl ratio and lower amounts of ferulic acid dimers and trimers. High proportions of ether-linked phenolic acids (released by alkali at 170 °C) were detected specifically in the seed coat and tissues in the crease region. The possible application of biochemical markers found in the various tissues to monitor wheat grain fractionation processes is discussed.     

Effects of fermentation and heat treatments on bound-ferulic acid content and total antioxidant capacity of bread crust-like systems made of different whole grain flours

In this study, bread crust-like systems were prepared by heating (5, 15 and 30 min at 200 °C) freeze-dried fermented doughs obtained using different cereal grains. The flours of whole wheat, refined wheat, whole einkorn, whole rye, whole oat and whole maize were used. The effects of fermentation and heating on bound ferulic acid concentration and total antioxidant capacity were determined. Besides, high molecular weight fractions, containing also melanoidins formed in bread crust-like systems during heating were analyzed for their bound ferulic acid content and total antioxidant capacity. Increasing heating time at 200 °C also increased the amounts of high molecular weight fractions in the bread crust-like systems for all cereals. The total antioxidant capacity of bread crust-like samples increased significantly with heating time (p < 0.05). However, the opposite was true for the high molecular weight fractions of bread crust-like samples. Mean bound ferulic acid concentrations of different cereal flours were found to range between 78.3 mg/kg (for refined wheat) and 667.7 mg/kg (for whole einkorn). Heating had no significant effect on bound ferulic acid contents of bread crust-like systems. For all cereals, the highest concentrations of bound ferulic acid were detected in the high molecular weight fractions of bread crust-like systems heated at 200 °C for 5 min. However, bound ferulic acid concentrations significantly decreased in high molecular weight fractions as heating time increased (p < 0.05).     

Ascorbate Oxidase levels in Wheat and their Relationship to Baking Quality

Flour samples from 127 samples of wheat of 13 different cultivars grown throughout New Zealand during two seasons were extracted with 1mNa₂SO₄(pH 8·3) and assayed for ascorbate oxidase (AOX) at pH 6·2 by a continuous spectrophotometric method. The mean AOX activity of the cultivar with the greatest activity, Domino, was more than three times that of the cultivar with the lowest activity, Brock. The differences in AOX activity amongst cultivars were maintained for two seasons. The range of AOX activities of different wheat samples within each cultivar was about two-fold for most cultivars. A sample of cv. Domino with the highest activity was 14 times more active than the lowest activity sample of cv. Brock. There was a significant correlation between low AOX activity and bake score of cultivars or individual wheat samples. There was also a correlation between log AOX and protein content, and protein content was also correlated with bake score. Flour stored for 300 days at 20°C and wheat stored for two or more years had reduced AOX activities and bake scores. However, flour containing low endogenous AOX activity produced the same bake scores with ascorbic acid plus squash AOX as with ascorbic acid alone. It was concluded that the level of AOX in wheat was not critical to the ascorbic acid improver effect, provided sufficient oxygen was mixed into the dough by high-speed mixers.     

Phenolic antioxidant-linked anti-hyperglycemic properties of rye cultivars grown under conventional and organic production systems

Rye (Secale cereale L.), is a temperate cereal food crop with diverse human health benefits partly linked to phenolic bioactives. Therefore targeting rye cultivars rich in phenolic bioactives and associated antioxidant properties has relevance to develop dietary support against chronic diseases, such as hyperglycemia linked to progression of type 2 diabetes. In this study we screened 9 rye cultivars and compared the impact of two different production practices (conventional and organic) on phenolic bioactive associated antioxidant and anti-hyperglycemic properties using in vitro assay models. Total soluble phenolic content (TSP), phenolic acids profile, protein content, antioxidant activity (AA), and hyperglycemia relevant α-amylase and α-glucosidase enzyme inhibitory activities of aqueous extracts of rye cultivars were evaluated using in vitro models. Overall, rye grown under organic production had higher yield, 1000 kernel weight, α-amylase inhibitory activity, and ferulic and benzoic acid content. On the contrary rye grown under conventional production had higher TSP content, AA, and α-glucosidase enzyme inhibitory activity. Further significant differences in phenolic antioxidant-linked anti-hyperglycemic properties among 9 rye cultivars were observed. This study indicated that differences in cultivars and production practices had significant impact on human health relevant phenolic antioxidant and associated anti-hyperglycemic properties of rye cultivars.